DE3525363A1 - Verfahren zur herstellung von auf wedelolacton- und/oder desmethylwedelolacton standardisierten extrakten aus eclipta alba und verwendung der extrakte zur herstellung eines lebertherapeutikums - Google Patents
Verfahren zur herstellung von auf wedelolacton- und/oder desmethylwedelolacton standardisierten extrakten aus eclipta alba und verwendung der extrakte zur herstellung eines lebertherapeutikumsInfo
- Publication number
- DE3525363A1 DE3525363A1 DE19853525363 DE3525363A DE3525363A1 DE 3525363 A1 DE3525363 A1 DE 3525363A1 DE 19853525363 DE19853525363 DE 19853525363 DE 3525363 A DE3525363 A DE 3525363A DE 3525363 A1 DE3525363 A1 DE 3525363A1
- Authority
- DE
- Germany
- Prior art keywords
- desmethylwedelolactone
- wedelolactone
- extracts
- standardized
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- LUTYTNLPIUCKBJ-UHFFFAOYSA-N Demethylwedelolactone Chemical compound O1C2=CC(O)=C(O)C=C2C2=C1C1=C(O)C=C(O)C=C1OC2=O LUTYTNLPIUCKBJ-UHFFFAOYSA-N 0.000 title claims abstract description 49
- RFQPHWCAHNTCDX-UHFFFAOYSA-N wedelolactone Natural products COc1cc(O)cc2OC(=O)c3c(oc4cc(O)c(O)cc34)c12 RFQPHWCAHNTCDX-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000000284 extract Substances 0.000 title claims abstract description 24
- 244000286838 Eclipta prostrata Species 0.000 title claims abstract description 22
- XQDCKJKKMFWXGB-UHFFFAOYSA-N wedelolactone Chemical compound O1C2=CC(O)=C(O)C=C2C2=C1C1=C(O)C=C(OC)C=C1OC2=O XQDCKJKKMFWXGB-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract 5
- 210000004185 liver Anatomy 0.000 title claims description 12
- 230000001225 therapeutic effect Effects 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 13
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000006286 aqueous extract Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 230000001929 anti-hepatotoxic effect Effects 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000011251 protective drug Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 230000029087 digestion Effects 0.000 abstract 1
- 238000010812 external standard method Methods 0.000 abstract 1
- 230000002443 hepatoprotective effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 8
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 8
- 239000002038 ethyl acetate fraction Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 210000003494 hepatocyte Anatomy 0.000 description 5
- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 101710098398 Probable alanine aminotransferase, mitochondrial Proteins 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- FDQAOULAVFHKBX-UHFFFAOYSA-N Isosilybin A Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC(=CC=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-UHFFFAOYSA-N 0.000 description 3
- 206010023126 Jaundice Diseases 0.000 description 3
- 230000006819 RNA synthesis Effects 0.000 description 3
- VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 244000063471 Wedelia calendulacea Species 0.000 description 3
- 210000003855 cell nucleus Anatomy 0.000 description 3
- 229940078979 liver therapy drug Drugs 0.000 description 3
- 239000000401 methanolic extract Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229940043175 silybin Drugs 0.000 description 3
- 235000014899 silybin Nutrition 0.000 description 3
- 229950010342 uridine triphosphate Drugs 0.000 description 3
- 206010067125 Liver injury Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229930002875 chlorophyll Natural products 0.000 description 2
- 235000019804 chlorophyll Nutrition 0.000 description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 231100000234 hepatic damage Toxicity 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 230000008818 liver damage Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229920002477 rna polymer Polymers 0.000 description 2
- 229960004245 silymarin Drugs 0.000 description 2
- 235000017700 silymarin Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000272459 Silybum marianum Species 0.000 description 1
- 235000010841 Silybum marianum Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- PGAVKCOVUIYSFO-XVFCMESISA-N UTP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 PGAVKCOVUIYSFO-XVFCMESISA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 230000003082 hepatotoxic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000001543 purgative effect Effects 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000008030 superplasticizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- PGAVKCOVUIYSFO-UHFFFAOYSA-N uridine-triphosphate Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)OC1N1C(=O)NC(=O)C=C1 PGAVKCOVUIYSFO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853525363 DE3525363A1 (de) | 1985-07-16 | 1985-07-16 | Verfahren zur herstellung von auf wedelolacton- und/oder desmethylwedelolacton standardisierten extrakten aus eclipta alba und verwendung der extrakte zur herstellung eines lebertherapeutikums |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853525363 DE3525363A1 (de) | 1985-07-16 | 1985-07-16 | Verfahren zur herstellung von auf wedelolacton- und/oder desmethylwedelolacton standardisierten extrakten aus eclipta alba und verwendung der extrakte zur herstellung eines lebertherapeutikums |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3525363A1 true DE3525363A1 (de) | 1987-01-22 |
| DE3525363C2 DE3525363C2 (enrdf_load_stackoverflow) | 1989-09-28 |
Family
ID=6275898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853525363 Granted DE3525363A1 (de) | 1985-07-16 | 1985-07-16 | Verfahren zur herstellung von auf wedelolacton- und/oder desmethylwedelolacton standardisierten extrakten aus eclipta alba und verwendung der extrakte zur herstellung eines lebertherapeutikums |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3525363A1 (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006699A1 (en) * | 1990-10-12 | 1992-04-30 | The Procter & Gamble Company | Plant extracts as mucosal-protective agents |
| US5130133A (en) * | 1990-09-28 | 1992-07-14 | The Procter & Gamble Company | Plant extracts as mucosal-protective agents |
| FR2679134A1 (fr) * | 1991-07-19 | 1993-01-22 | Sablon Louis | Compositions cosmetiques pour la regulation de la pigmentation cutanee comprenant un extrait d'eclipta alba. |
| CN102716167A (zh) * | 2012-07-13 | 2012-10-10 | 金莲锦 | 旱莲草的提取分离方法，该方法分离得到的提取物及用途 |
| CN103235082A (zh) * | 2013-04-27 | 2013-08-07 | 贵州盛世龙方制药股份有限公司 | 精乌胶囊的检测方法 |
| CN104045648A (zh) * | 2013-03-13 | 2014-09-17 | 中国科学院大连化学物理研究所 | 一种规模化制备蟛蜞菊内酯化学对照品的方法 |
| CN109991347A (zh) * | 2017-12-30 | 2019-07-09 | 苏州唐锟辰新能源科技有限公司 | 一种墨旱莲药材的hplc指纹图谱建立方法 |
-
1985
- 1985-07-16 DE DE19853525363 patent/DE3525363A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| Sci. Pharm. 49, 1981, S.262-264 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5130133A (en) * | 1990-09-28 | 1992-07-14 | The Procter & Gamble Company | Plant extracts as mucosal-protective agents |
| WO1992006699A1 (en) * | 1990-10-12 | 1992-04-30 | The Procter & Gamble Company | Plant extracts as mucosal-protective agents |
| FR2679134A1 (fr) * | 1991-07-19 | 1993-01-22 | Sablon Louis | Compositions cosmetiques pour la regulation de la pigmentation cutanee comprenant un extrait d'eclipta alba. |
| WO1993001796A1 (fr) * | 1991-07-19 | 1993-02-04 | Louis Emmanuel Sablon | Compositions cosmetiques contenant un extrait d'eclipta alba ____________________________________________________________ |
| US5559146A (en) * | 1991-07-19 | 1996-09-24 | Sablon; Lewis E. | Method of using cosmetic compositions comprising an extract of eclipta alba |
| CN102716167A (zh) * | 2012-07-13 | 2012-10-10 | 金莲锦 | 旱莲草的提取分离方法，该方法分离得到的提取物及用途 |
| CN104045648A (zh) * | 2013-03-13 | 2014-09-17 | 中国科学院大连化学物理研究所 | 一种规模化制备蟛蜞菊内酯化学对照品的方法 |
| CN104045648B (zh) * | 2013-03-13 | 2016-08-03 | 中国科学院大连化学物理研究所 | 一种规模化制备蟛蜞菊内酯化学对照品的方法 |
| CN103235082A (zh) * | 2013-04-27 | 2013-08-07 | 贵州盛世龙方制药股份有限公司 | 精乌胶囊的检测方法 |
| CN109991347A (zh) * | 2017-12-30 | 2019-07-09 | 苏州唐锟辰新能源科技有限公司 | 一种墨旱莲药材的hplc指纹图谱建立方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3525363C2 (enrdf_load_stackoverflow) | 1989-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |